1173184-14-9

Basic information

• Product Name: trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride
• Synonyms: trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride
• CAS NO: 1173184-14-9
• Molecular Weight: 305.804
• Mol File: 1173184-14-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride(1173184-14-9)
• EPA Substance Registry System: trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride(1173184-14-9)

Safety Data

• Hazardous Substances Data: 1173184-14-9(Hazardous Substances Data)

Upstream product

• 33996-30-4 trans-4-hydroxy-L-proline ethyl ester hydrochloride 
• 100-58-3 phenylmagnesium bromide 
• 51-35-4 4R-4-hydroxyproline 
• 108-86-1 bromobenzene 
• 176747-44-7 (2S,4R)-4-hydroxy-α,α-diphenyl-2-pyrrolidinemethanol 

Downstream Products

• 1173035-69-2 O-(2-methacryloyloxyethylsuccinoyl)-trans-4-hydroxy-α,α-di-phenyl-L-prolinol hydrochloride 
• 344791-02-2 (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester 
• 1198800-73-5 3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide 

Relevant articles and documents

Asymmetric reduction of ketones catalyzed by α,α-diphenyl-(L)-prolinol modified with imidazolium ionic liquid and BH3·SMe2 as a recoverable catalyst

The synthesis of α,α-diphenyl-4-trans-hydroxy-(L)-prolinol modified with imidazolium based ionic liquids was carried out with trans-α,α-diphenyl-4-hydroxy-(L)-prolinol, 5-bromovaleric acid or 1,5-dibromopentane and imidazole. α,α-Diphenyl-4-hydroxy-(L)-prolinol modified with imidazolium ionic liquid was treated with BH3·SMe2 which generate 1,3,2-oxazaborolidine, that acts as a catalyst for asymmetric reduction of prochiral ketones. α,α-Diphenyl-4-hydroxy-(L)-prolinol modified with imidazolium ionic liquids (PF6 anion) with BH3?SMe2 found to be an efficient catalyst (10 mol%) for the reduction of the acetophenone, gave 99% yield and 87-84% ee. The catalytic method has wide applicability for a variety of substrates. 1,3,2-oxazaborolidine containing ether linkage ionic liquid was recovered and reused up to 4 cycles with 99-91% yields and 87-81% ee's.

A general approach for preparation of polymer-supported chiral organocatalysts via acrylic copolymerization

(Figure Presented) Polymer-supported chiral organocatalysts, as well as most other forms of immobilized catalysts, are traditionally prepared by a postmodification approach where modified catalyst precursors are anchored onto prefabricated polymer beads. Herein, we report an alternative and more scalable approach where polymer-supported chiral enamine and iminium organocatalysts are prepared in a bottom-up fashion where methacrylic functional monomers are prepared in an entirely nonchromatographic manner and subsequently copolymerized with suitable comonomers to give cross-linked polymer beads. All syntheses have been conducted on multigram scale for all intermediates and finished polymer products, and the catalysts have proven successful in reactions taking place in solvents spanning a wide range of solvent polarity. While polymer-supported proline and prolineamides generally demonstrated excellent results and recycling robustness in asymmetric aldol reactions of ketones and benzaldehydes, the simplest type of Joargensen/Hayashi diarylprolinol TMS-ether showed excellent selectivity, but rather sluggish reactivity in the Enders-type asymmetric cascade. The polymer-supported version of the first-generation MacMillan imidazoHdinone had a pattern of reactivity very similar to that of the monomeric catalyst, but is too unstable to allow recycling.